Synthesis of functionalized biaryl compounds via ring expansion of alkenylcyclobutenones

Tetrahedron Letters

Volumn 44, Issue 1, 2003, Pages 167-170

  Hamura, Toshiyuki ^a   Morita, Masato ^a   Matsumoto, Takashi ^a   Suzuki, Keisuke ^a  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENYL GROUP; AROMATIC COMPOUND; KETONE DERIVATIVE; LITHIUM DERIVATIVE; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; METHODOLOGY; TEMPERATURE;

EID: 0037213001     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(02)02473-5     Document Type: Article

References (24)

1. For recent reviews, see: (a) Bringmann, G.; Breuning, M.; Tasler, S. Synthesis 1999, 525-558; (b) Bringmann, G.; Walter, R.; Weirich, R. Angew. Chem., Int. Ed. Engl. 1990, 29, 977-991; (c) Stanforth, S. P. Tetrahedron 1998, 54, 263-303; (d) Anctil, E. J.-G.; Snieckus, V. J. Organomet. Chem. 2002, 653, 150-160.
2. For recent reviews, see: (a) Bringmann, G.; Breuning, M.; Tasler, S. Synthesis 1999, 525-558; (b) Bringmann, G.; Walter, R.; Weirich, R. Angew. Chem., Int. Ed. Engl. 1990, 29, 977-991; (c) Stanforth, S. P. Tetrahedron 1998, 54, 263-303; (d) Anctil, E. J.-G.; Snieckus, V. J. Organomet. Chem. 2002, 653, 150-160.
3. For recent reviews, see: (a) Bringmann, G.; Breuning, M.; Tasler, S. Synthesis 1999, 525-558; (b) Bringmann, G.; Walter, R.; Weirich, R. Angew. Chem., Int. Ed. Engl. 1990, 29, 977-991; (c) Stanforth, S. P. Tetrahedron 1998, 54, 263-303; (d) Anctil, E. J.-G.; Snieckus, V. J. Organomet. Chem. 2002, 653, 150-160.
4. For recent reviews, see: (a) Bringmann, G.; Breuning, M.; Tasler, S. Synthesis 1999, 525-558; (b) Bringmann, G.; Walter, R.; Weirich, R. Angew. Chem., Int. Ed. Engl. 1990, 29, 977-991; (c) Stanforth, S. P. Tetrahedron 1998, 54, 263-303; (d) Anctil, E. J.-G.; Snieckus, V. J. Organomet. Chem. 2002, 653, 150-160.
5. Recently, we developed a new synthetic method of hindered 1-arylnaphthalene derivatives via ring expansion of benzocyclobutenones, see: Hamura T., Miyamoto M., Matsumoto T., Suzuki K. Org. Lett. 4:2002;229-232.
6. Formation of six-membered ring carbocycles in this type of reactions: (a) Liu, F.; Liebeskind, L. S. J. Org. Chem. 1998, 63, 2835-2844; (b) Morwick, T. M.; Paquette, L. A. J. Org. Chem. 1997, 62, 627-635; (d) Taing, M.; Moore, H. W. J. Org. Chem. 1996, 61, 329-340; (d) Perri, S. T.; Moore, H. W. J. Am. Chem. Soc. 1990, 112, 1897-1905; (e) Danheiser, R. L.; Gee, S. K.; Perez, J. J. J. Am. Chem. Soc. 1986, 108, 806-810.
7. Formation of six-membered ring carbocycles in this type of reactions: (a) Liu, F.; Liebeskind, L. S. J. Org. Chem. 1998, 63, 2835-2844; (b) Morwick, T. M.; Paquette, L. A. J. Org. Chem. 1997, 62, 627-635; (d) Taing, M.; Moore, H. W. J. Org. Chem. 1996, 61, 329-340; (d) Perri, S. T.; Moore, H. W. J. Am. Chem. Soc. 1990, 112, 1897-1905; (e) Danheiser, R. L.; Gee, S. K.; Perez, J. J. J. Am. Chem. Soc. 1986, 108, 806-810.
8. Formation of six-membered ring carbocycles in this type of reactions: (a) Liu, F.; Liebeskind, L. S. J. Org. Chem. 1998, 63, 2835-2844; (b) Morwick, T. M.; Paquette, L. A. J. Org. Chem. 1997, 62, 627-635; (d) Taing, M.; Moore, H. W. J. Org. Chem. 1996, 61, 329-340; (d) Perri, S. T.; Moore, H. W. J. Am. Chem. Soc. 1990, 112, 1897-1905; (e) Danheiser, R. L.; Gee, S. K.; Perez, J. J. J. Am. Chem. Soc. 1986, 108, 806-810.
9. Formation of six-membered ring carbocycles in this type of reactions: (a) Liu, F.; Liebeskind, L. S. J. Org. Chem. 1998, 63, 2835-2844; (b) Morwick, T. M.; Paquette, L. A. J. Org. Chem. 1997, 62, 627-635; (d) Taing, M.; Moore, H. W. J. Org. Chem. 1996, 61, 329-340; (d) Perri, S. T.; Moore, H. W. J. Am. Chem. Soc. 1990, 112, 1897-1905; (e) Danheiser, R. L.; Gee, S. K.; Perez, J. J. J. Am. Chem. Soc. 1986, 108, 806-810.
10. Formation of six-membered ring carbocycles in this type of reactions: (a) Liu, F.; Liebeskind, L. S. J. Org. Chem. 1998, 63, 2835-2844; (b) Morwick, T. M.; Paquette, L. A. J. Org. Chem. 1997, 62, 627-635; (d) Taing, M.; Moore, H. W. J. Org. Chem. 1996, 61, 329-340; (d) Perri, S. T.; Moore, H. W. J. Am. Chem. Soc. 1990, 112, 1897-1905; (e) Danheiser, R. L.; Gee, S. K.; Perez, J. J. J. Am. Chem. Soc. 1986, 108, 806-810.
11. (a) Danheiser R.L., Sard H. Tetrahedron Lett. 24:1983;23-26.
12. (b) Danheiser R.L., Savariar S. Tetrahedron Lett. 28:1987;3299-3302.
13. (c) Danheiser, R. L.; Savariar, S.; Cha, D. D. Organic Synthesis, Wiley, New York, 1993, Collect. Vol. VIII, pp. 82-86.
14. (d) Hassner A., Dillon J.L. Jr. J. Org. Chem. 48:1983;3382-3386.
15. Hamura T., Kakinuma M., Tsuji S., Matsumoto T., Suzuki K. Chem. Lett. 2002;748-749.
16. Hamura T., Kawano N., Tsuji S., Matsumoto T., Suzuki K. Chem. Lett. 2002;1042-1043.
17. (a) Rondan N.G., Houk K.N. J. Am. Chem. Soc. 107:1985;2099-2111.
18. (b) Houk K.N., Spellmeyer D.C., Jefford C.W., Rimbault C.G., Wang Y., Miller R.D. J. Org. Chem. 53:1988;2125-2127.
19. (c) Nakamura K., Houk K.N. J. Org. Chem. 60:1995;686-691.
20. (d) Niwayama S., Kallel E.A., Spellmeyer D.C., Sheu C., Houk K.N. J. Org. Chem. 61:1996;2813-2825.
21. The attempts at an anion-accelerated cyclization of lithium enolate 5 were unfruitful. Heating of the silyl ether 5′ also gave no cyclized product.
22. We thank Dr. Akiko Sekine, Tokyo Institute of Technology, for X-ray analysis. The ORTEP drawing of 7d is shown below. Crystallographic data reported in this paper have been deposited with Cambridge Crystallographic Data Centre as supplementary publication no. CCDC-193917. Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge, CB2 1EZ, UK (fax: (+44)1223-336-033; e-mail: deposit@ccdc.cam.ac.uk).
23. In most cases, thermal reactions of the corresponding ethyl carbonate 7, prepared by the reaction of the lithium trienolate with ethyl chloroformate, proceeded smoothly to give the corresponding biaryls in high yields. For example, heating of 7h in DMSO at 155°C gave 8h in 91% yield. This protocol was attractive in that the reaction can be performed under neutral conditions. However, the reaction of sterically congested substrate 7i, again, gave the lower yield of product (see below).
24. 11.3-Pyridyllithium was generated by halogen-lithium exchange of the corresponding bromopyridine and n-BuLi (THF, -78°C).